Reductive Lithiation of Methyl Substituted Diarylmethylsilanes: Application to Silanediol Peptide Precursors
Reductive Lithiation of Methyl Substituted Diarylmethylsilanes: Application to Silanediol Peptide Precursors
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DOI：
10.1021/ol102968g
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发表时间：
2011-02-18
期刊：
影响因子：
5.2
通讯作者：
Skrydstrup, Troels
中科院分区：
文献类型：
--
作者：
Hernandez, Dacil;Mose, Rasmus;Skrydstrup, Troels
用萘化锂还原锂化甲基二芳基甲基硅烷是制备相应硅基锂试剂的一种实用方法。它们与手性亚磺胺的加成提供了硅烷醇和硅烷二醇的多种前驱体。用更不稳定的二芳基硅烷部分取代目前使用的二苯基硅烷基元，可以通过TFA处理选择性地水解一个或两个芳基。
Reductive lithiation of methyl-substituted diarylmethylsilanes using lithium naphthalenide represents a practical method for the preparation of the corresponding sillyl lithium reagents. Their addition to chiral sulfinimines affords versatile precursors to silanols and silanediols. The replacement of the currently used diphenylsilane motif by a more labile diarylsilane moiety allows the selective hydrolysis of one or two aryl groups by treatment with TFA.